Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate

HRID 1372674

反応式

HRID 1372674 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[Cl:24].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[Cl:24][C:14]1[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

参加物

5

反応物 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 117084142-bromo-6-methylbenzo[d]thiazoleHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

生成物 1

HCID 58778443Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate収率 26%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

In xylene (10 ml), 2-bromo-6-methylbenzothiazole (703 mg, 3.08 mmol), methyl 4-amino-3-chlorophenylacetate (615 mg, 3.08 mmol), and pyridinium p-toluenesulfonate (PPTS) (232 mg, 0.92 mmol) were heated under reflux for 10 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1, v/v) eluate fractions, methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate (274 mg, 26%) was obtained as a pale yellow solid.

後処理

  1. temperatureunder reflux for 10 hours
  2. temperatureAfter cooling
  3. distillationthe reaction mixture was distilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1

出典と根拠

ORDレコード
ord-5ed36a50cb3947d499c75b1a568ec65e
出典データセット
uspto-grants-2007_01
特許番号
US07157487B2

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